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Total synthesis of Mycestericin E:
Reference: Iwabuchi, Y.; Furukawa, M.; Esumi, T.; Hatakeyama, S. Chem. Commun. 2001, 2030. DOI
Keywords: CarboxEster -> Alkyl-OH • O-H -> O-SiPh2tBu • Alkyl-OH -> Aldehyde-α-NR2 • Pinnick oxidation • Aldehyde -> CarboxAcid • O-SiPh2tBu -> O-H • Ketal -> Ketone • N-C(O)OR -> N-H • Epoxidation, nucleophilic EnoateEster • Ritter - epoxide • Li/H -> Li-Dithiane • Li/H -> Li-Alkynyl • Ketal(thio) -> Ketone • O-SiMe2tBu -> O-H • Ketone -> Ketal • Alkyl-OH -> Aldehyde • Li-Dithiane+Alkyl-X • Li-Alkynyl+Alkyl-X • Alkyne -> Ene-trans • Morita-Bayliss-Hillman(asym) •
Reagents: NaOMe • Hydroperoxide, tbutyl - Ti(OiPr)4 • BH4-Na+ • SiPh2tBu-Cl • DBU • DMSO, (COCl)2 • Chlorite, sodium • Diazomethane • BF3·OEt2 • HF • Hydroxide, sodium • Chiral catalyst • Acetonitrile, trichloro • Epoxide • BuLi(n) • Alkynyl-Li • MeI • TsOH • AlH4-Li+ • DMSO, (COCl)2 • Chiral catalyst • Acrylate •

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